ESPN insider Shams Charania has reported that the Boston Celtics have traded all-star guard Jrue Holiday to the Portland Trail Blazers in exchange for Anfernee Simons and two second round picks. What does this move mean for Boston and what move could GM Brad Stevens make next? Chat Sports host Tyler Smith breaks it all down on this Boston Celtics YouTube video.
In a late-night shocker that few saw coming, the Boston Celtics have traded veteran guard Jrue Holiday to the Portland Trail Blazers in exchange for 26-year-old Anfernee Simons and two second-round picks. The blockbuster move, executed quietly by Celtics President of Basketball Operations Brad Stevens, marks the first major domino to fall for Boston in what promises to be an aggressive offseason.
The deal comes just months after Holiday played a critical role in the Celtics’ 2024 NBA championship run, making the trade both surprising and significant. While rumors had long circulated that the Celtics were looking to shed salary due to looming second-apron tax implications, no one anticipated a Simons-for-Holiday swap.
What Boston Gets
Anfernee Simons arrives in Boston with plenty of upside. The 6’3″ guard has quietly been one of the few bright spots on an otherwise struggling Portland team. Averaging over 19 points per game each of the past two seasons, Simons brings a scoring punch and offensive versatility that should slot in nicely alongside Jayson Tatum and Jaylen Brown.
While questions remain about Simons’ defense, Boston’s structured system under head coach Joe Mazzulla could be the perfect environment to unlock his potential on both ends of the floor. More importantly, Simons fits Boston’s timeline. At 26, he’s entering his prime and can complement the Celtics’ young core while offering salary relief in the short term.
Financially, Simons is owed $25.9 million next season, which is less than Holiday’s $32.4 million salary. The deal offers the Celtics some modest short-term relief and helps them maneuver under the league’s punitive second apron in future years.
Why Boston Made the Deal
The Celtics’ salary sheet is bloated, and Stevens had made it clear: moves were coming. Holiday, though beloved for his poise, defense, and championship contributions, was viewed as a luxury Boston could no longer afford. He is 34 years old and under contract for two more seasons at an expensive rate.
While some insiders believed Boston would need to attach a first-round pick to unload Holiday’s deal, Stevens instead landed a younger, starting-caliber guard and picks. That’s a clear win in terms of asset management.
ESPN’s Bobby Marks estimates the Celtics could save as much as $40 million in tax penalties with this trade. With Simons on a more manageable contract and set to expire next offseason, Boston retains flexibility while staying competitive.
The Portland Angle
For the Blazers, the return of Holiday is a curious but potentially strategic move. Holiday, who briefly belonged to Portland last offseason before being flipped to Boston in the Damian Lillard trade, may not stay long this time either. Multiple sources have suggested the Blazers could reroute Holiday again before the season begins.
If Portland keeps Holiday, it suggests an organizational pivot toward competitiveness around young star Scoot Henderson. If not, expect them to shop Holiday for more draft capital or veteran depth.
What’s Next for Boston?
According to NBA insider Shams Charania, Boston’s front office is “extremely active” and still engaged in trade talks involving several players, including Kristaps Porziņģis and sharpshooter Sam Hauser. Both are viewed as potential salary-dump candidates as the Celtics attempt to retool around Tatum and Brown without exceeding cap thresholds.
There’s also speculation that teams may come calling for Derrick White, fresh off a strong playoff performance. White, still under contract, could command a massive return given how highly the Celtics value him.
While a Jaylen Brown trade seems unlikely at the moment, the Celtics have made it clear they are listening to all offers. Boston has just days before the 2025 NBA Draft to potentially execute more moves, and the front office is expected to stay active.
The Verdict
Celtics fans may be surprised or even saddened by Holiday’s departure, especially after his clutch postseason moments. But this trade balances basketball value, future flexibility, and financial responsibility.
Anfernee Simons is not just a salary swap—he’s a dynamic scorer who could flourish in Boston’s winning environment. And with two second-round picks added to Brad Stevens’ growing war chest, the Celtics aren’t just cutting costs—they’re planning for sustained contention.
Grade this trade? It looks like a solid A- for Boston—for now. And as the offseason unfolds, don’t be surprised if this is only the beginning.
